Green to black vat dyestuff.



Ph.. D., chemist, and Rronaau L many, and

VUNITED STATES PATENT ornrcE,

KARL SGHIRMACHER, or riccnsr-on-rnn-mam, AND mdmmn rnoromi-lor nocn- HEIM-ON-THE-MAIN, GERMANY, ASSIGNORS T0 mnnwmugn vonm. mmsrnn y LUCIUS a nntmme, or HocnsnoN-rHnMam, GERMANY, A conrona'rrorror GERMANY. a

GREEN To BLACK VAT DYE$TUFF. 1,001,457, Specification of Letters Patent. 1T0 Drawing. Application med October 3, 1910. Serial No. To all whomit may concern: J Be it known that we, KARL fSczgxan-aomm,

firhnn, Ph. D., cheniist, citizens of the Em p'ireof Germany, residin at Hochst-on-the-Main, Gerochh'eim on the Main Germany, respectively, have invented/certain, new and useful Improvements in Green to Black Vat Dyestuffs, of which the following i is a specification. I

W'hereas, by introducing substituents 'into the thioindigo molecule, -it isv possible to .Vary the tints of the dyestuffs of the thinindigo series from orange to black, this quality has not-been observed in the dyestuffs. of the indigo series, the color of all the indigo derivatives hitherto known being blue or purple. Now, .we have .found that are obtained by inmolccule in the' meta position to the-ni trogen. Such indigo derivatives are" obtained by subjectingto oxidation those in doxyl derivatives which can be produced fromfi-alkylthio F phenyl 1 glycin 2 carboxyli'c acid, and they are dark-green to black vat dyestuifs' which can be easily reduced to vats and dye in the vatcottonand wool fast tints.- a

follows:

The formula of the new dyestuffs is-as The following example illustrates our invention; 100'parts' by weight of the acid I alizfl.

'sodium Salt of 5-ethylth ophenyl 1-gly-- produced "by the ac crin-Q-carbqx'ylie acid, tion of chloracetic acid on ethylthio-an thranilic acidv (described in" French Patent N0, as4,t1s

Patented Aug. 22, 1911. 585,120

fluxvapparatus. After the mass has cooled it is added to about times-its qiiantity of water. The mixtureis then rendered caustic-alkaline with caustic soda lye and heated, while well stirring and blowin air 1nto-the caustic-alkaline solution, unti the' dyestufi is completely separated.

The dyestufl' is when dry :1 dark grenishblack powder, soluble in concentratedsulfuric'acid hue, soluble in glacial acetic acid with a. green and-in alcohol and nitrobenzem with a red coloration of agreen dichroisr'n; it is readily'reducible and dyes cotton and wool in'the vat, air. green to black tints. Having now particularly described our invention, what we 'claim is:

As new derivatives of indigo,

mud or glacial acetic acid with a green 'coloration and yielding a dichroistic solution of a brownis soluble in alkaline hydrosulfite with low color and dyeing cotton and wool to'black tints.

2.,As a new :1 ye]- green product, the 6.6diethylthio derivative of indi o, being a greenish black powder, solub e in concentrated su'l-' furic acid with a bluish-green coloration, in

glacial acetic acid with a green coloration and yielding in a-lcohol or nitmbenzene -a gdichroistic solution of' a brewuish-rcd to 85 green coloration, readily soluble in alkaline hy'drosulfite witha yellow coloration and dyeing cotton and wool'green to hiaclrtints.

In testimony whereof, we aili tures in presence oftwo wit-near: v

KARLSCHIRM RICHARD LEE Witnessesr F JEAN'GRUND, CARL Gnrmn.

are heated to boiling for a short time with about 500 parts of acetic anhydrid in a re- 50 witha green coloration of a blue with subsequent oxidation in the products' the 6.6dia1ky'lthi being greenish-black 79' powders, sol uble in concentrated sulfuric -red to green color when dis-' l solved .in alcohol or nitrobenzene, readily 751. 

